The next answers were provided by Passionofthemom and Baygirl. They outdid my answers. The I could do was 3 moves for the first one and 4 for the second one. Congrats to them both.

Link: Jude Law to Joaquin Phoenix2 moves: Jude Law in Cold Mountain with Nicole Kidman in To Die For with Joaquin Phoenix.Or Jude Law in Talented Mr Ripley with Gwyneth Paltrow in Two Lovers with Joaquin Phoenix

Link: Goldie Hawn to Pauly Shore2 moves: Goldie Hawn in Town & Country with Nastassja Kinski in Red Letters with Pauly Shore.